Methyl 4-(p-chlorophenoxy)butyrate → HCID 178508402, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-(4-chlorophenoxy)butanoate (1.4 g, 6.13 mmol), aminoguanidine bicarbonate (2.08 g, 15.3 mmol), and pyridine (12 mL) was added to a 100 mL RBF with a magnetic stirring bar. The flask was fitted with a condenser, and heated to 125° C. using an oil bath. Progress of the reaction was monitored by analytical HPLC with UV detection at 215 nm. The mixture was heated for 20 hours, and an additional portion of aminoguanidine bicarbonate (0.60 g, 4.4 mmol) was added. After an additional 22 hours of heating, the reaction was complete. The reaction allowed to cool to ambient temperature, concentrated under reduced pressure and partitioned between ethyl acetate (50 mL) and water (20 mL). The aqueous layer was extracted once more with ethyl acetate (30 mL). The combined organic layers were washed with saturated aqueous NaCl (2×15 mL), dried (Na2SO4), filtered and concentrated. Dichloromethane (5 mL) was added and a precipitate that formed was isolated by filtration, rinsed with dichloromethane (5 mL), and then dried under reduced pressure to afford the title compound as a white powder (1.12 g, 72% yield).

Provenance & Evidence